I grew up in a very small town (400 population) in central Illinois. Growing up, gay was used as a derogatory term.
Starting with 5th grade, we were bussed to the next town over (20,000 population) which also had a state university (10,000 students). The town was more open but still very conservative. There was a bar downtown that would open their basement to the gay/lesbian crowd on weekends. While I was in college, I helped start the first gay/lesbian/bi/trans/ally student union.
After college, I moved an hour north to Champaign/Urbana, which has about 130,000 population. Urbana is a bit more liberal than Champaign, but they both are very open and accepting. Both Champaign and Urbana were the first 2 towns in Illinois to pass gay discrimination laws. While we had 3 different gay bars at one time, there are no longer any gay bars, they all closed down because most of the bars and restaurants (downtown at least) are very gay-friendly. As long as I have lived here, the University of Illinois has always had different gay/lesbian groups. Each year Urbana hosts gay pride while Champaign has the gay pride parade.
I found the gay scene in Chicago to be amazing. It was very open and accepting when I lived there. Now I hear from friends that the neighborhood is getting sketchy and isn't always as safe as it was.
As for Chicago, we used to go there many times each year. Boystown used to be a great place to visit. Many gay businesses, restaurants and bars. It was the place to live for gay men. Now it is home to many straight people, not as gay as it used to be. It isn't the same as it used to be. We no longer go to Boystown, we usually spend our time in the suburbs, near the boyfriends family.